34271-27-7Relevant articles and documents
L-Methionine related 1-amino acids by acylase cleavage of their corresponding N-acetyl-DL-derivatives
Bommarius, Andreas S.,Drauz, Karlheinz,Guenther, Kurt,Knaup, Guenter,Schwarm, Michael
, p. 3197 - 3200 (2007/10/03)
Acylase I from Aspergillus oryzae is an even more useful enzyme than suggested so far. Besides standard amino acids such as L-Met, L-Val and L-Phe, a number of additional sulfur- and selenium-containing amino acids can be obtained at useful reaction rates and in very high enantiomeric purity by kinetic resolution of the respective N-acetyl-DL-amino acids.
Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I
Chenault, H. Keith,Dahmer, Juergen,Whitesides, George M.
, p. 6354 - 6364 (2007/10/02)
Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.
ASYMMETRISCHE KATALYSEN. XXX. ENANTIOSELEKTIVE HYDRIERUNG VON CROTONSAEUREDERIVATEN MIT RHODIUM-PHOSPHIN-KATALYSATOREN
Brunner, Henri,Knott, Alfons,Kunz, Manfred,Thalhammer, Elisabeth
, p. 55 - 62 (2007/10/02)
The Z- and E-isomers of the α-N-benzoylamino-2-butenoic acid methyl ester, the E/Z mixtures of α-N-benzoylamino-2-butenoic acid, and the Z-form of α-N-acetylamino-2-butenoic acid were hydrogenated enantioselectively.The hydrogenation products are derivatives of α-aminobutyric acid, which can be reduced to aminobutanol, the optically active component of the antituberculosis drug (+)-ethambutol.In situ catalysts consisting of 2 and the optically active phosphine ligands (+)- and (-)-Norphos, (+)-Prophos, (-)-Chiraphos, (-)-BPPFA, (-)-Diop, and (+)- and (-)-CpMn(CO)2diop were used.The best results were obtained with the substrate (Z)-α-acetylamino-2-butenoic acid and the catalyst 2/(-)-Norphos with 91.5percent e.e.